Professional allocators rarely receive feedback on their ability to question managers. Ted Seides found that hosting a podcast, which requires listening to and editing his own interviews, created an invaluable feedback loop that dramatically improved his information-gathering and due diligence skills.

Act as a strategic partner, not a vendor, by analyzing a prospect's annual reports, 10Ks, and shareholder letters. Use this research to inform them about strategic risks or business issues they haven't considered, immediately differentiating you from competitors who just ask basic discovery questions.

Effective due diligence isn't a checklist, but the collection of many small data points—revenue, team retention, customer love, CVC interest. A strong investment is a "beam" where all points align positively. Any misalignment creates doubt and likely signals a "no," adhering to the "if it's not a hell yes, it's a no" rule.

When evaluating talent, the biggest red flag is "hand-waving." If you ask a direct question about their area of responsibility and they can't give a crisp, clear explanation, they likely lack true understanding. Top performers know their craft and can explain the "why" behind their actions.

A candidate can claim they want growth, but their resume tells the real story. Scrutinize *why* they moved between specific companies. A move for a bigger salary versus a move to work under a renowned leader reveals their actual priorities far more accurately than their interview answers.

To elicit candid answers from fund managers, the most effective technique is not the question itself but the silence that follows. Resisting the psychological urge to fill the space forces the manager to sit with the question, often leading to less rehearsed and more truthful responses.

Instead of seeking feedback broadly, prioritize 'believability-weighted' input from a community of vetted experts. Knowing the track record, specific expertise, and conviction levels of those offering advice allows you to filter signal from noise and make more informed investment decisions.

The most driven entrepreneurs are often fueled by foundational traumas. Understanding a founder's past struggles—losing family wealth or social slights—provides deep insight into their intensity, work ethic, and resilience. It's a powerful, empathetic tool for diligence beyond the balance sheet.

Senior executives are, by definition, excellent at interviewing, making the process unreliable for signal. Instead of relying on a polished performance, ask to see the 360-degree performance reviews from their previous company. This provides a more honest, ground-truth assessment of their strengths and weaknesses.